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Vacation rentals in Pittsfield

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Travel insights for vacation rentals in Pittsfield

Use our HotelsCombined data-powered tips to help you find your next vacation rental in Pittsfield.

What is the cheapest day to stay in a vacation rental in Pittsfield?

The cheapest day to stay in Pittsfield is Thursday (C$ 196). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is C$ 454.

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Cheapest vacation rentals in Pittsfield, Massachusetts

Discover affordable stays in Pittsfield that provide a quality experience without breaking the bank. Hotels in Pittsfield can be found for as low as C$ 143 per night. There is currently one property in Pittsfield that can be booked for this price. Berkshire Mountain Lodge is one of the hotels that can be booked for the lowest price in Pittsfield. Price data was last updated on 28 June 2026
For those on a budget, these are the cheapest vacation rentals available in Pittsfield for the selected dates. Prices can differ depending on the dates selected, so use the search form to browse more options if you have flexibility.
Berkshire Mountain Lodge
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Pittsfield, MA, United States
4.4 km from city centre
Air Conditioning
C$ 143
Avg. per night
View Deal

Other accommodations in Pittsfield

Find the perfect vacation rental for your stay in Pittsfield. There are 61 hotels in Pittsfield and price data was last updated on 28 June 2026. The average price for a hotel in Pittsfield is .
Hotel on North
Hotel on North

Hotel on North

297 North Street, Pittsfield, MA, United States
0.7 km from city centre
Free Wi-Fi
Parking
C$ 230
Avg. per night
View Deal
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

1350 West Housatonic Street, Pittsfield, MA, United States
5.7 km from city centre
Free Wi-Fi
Parking
C$ 118
Avg. per night
View Deal
Berkshire Mountain Lodge
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Pittsfield, MA, United States
4.4 km from city centre
Air Conditioning
C$ 143
Avg. per night
View Deal
Berkshire Inn
Berkshire Inn

Berkshire Inn

150 West Housatonic Street, Pittsfield, MA, United States
1.6 km from city centre
Free Wi-Fi
Air Conditioning
C$ 122
Avg. per night
View Deal

Where to stay in Pittsfield

Explore different neighbourhoods and areas within Pittsfield to find the perfect location for your stay. Map data was last updated on 28 June 2026.
Navigate to the areas in Pittsfield you plan to visit to find vacation rentals that are close by. Users can click on a vacation rental's name to find more information about it, such as price, reviews, and amenities, and also find different deals for the property.

Facts about staying in Pittsfield

Find useful tips and insights about staying in Pittsfield to help you make the most of your experience. FAQs were last updated on 28 June 2026.

  • How much does a vacation rental in Pittsfield cost?

    Pittsfield vacation rentals are C$ 267/night on average. However, you may find that prices fluctuate depending on the time of year. For example, May is the most expensive month to book a vacation rental in Pittsfield, and January is often the cheapest month to book. Recently, our users found rentals for C$ 118/night - which is currently the cheapest price. Keep in mind that anything C$ 261/night or less is still considered a good deal.

  • Are there any Motel vacation rentals in Pittsfield?

    Yes, there are 5 Motel vacation rentals in Pittsfield. According to our data, Heart OF The Berkshires Motel is currently the most popular Motel rental in the city.

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